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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1425064Generated: October 26, 2026

Dimethylformamide → Methyl 3-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

https://huagongshe.com/reaction/1425064

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantMethyl 3-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateHCID 67548908—
CatalystZincHCID 23994—
CatalystTrichloroiron;hexahydrateHCID 16211236—
SolventWaterHCID 962—
ProductMethyl 3-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateHCID 6754906187.7%

Reaction Conditions

Temperature100 °C

Reaction Steps

DMF (5 mL), water (5 mL), zinc (0.7 g, 10.7 mmol) and iron trichloride hexahydrate (0.12 g, 0.4 mmol) were added to methyl 3-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate obtained in Example (100a) (0.35 g, 1.07 mmol), and the mixture was stirred at 100° C. for 50 minutes. The insoluble matter was filtered off and ethyl acetate was added to the mother liquor, and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave 0.28 g of the crude title compound as a brown oily substance (88%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08927588B2
Source datasetuspto-grants-2015_01
ORD IDord-2476bce55f1a439fa533f9ed571bca14
Source noteuspto-grants-2015_01